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A.R. Waterloo et al.
mixture was stirred under ambient conditions for 3 h at rt. The reaction solution was evapo-
rated to dryness, and the residue was precipitated from chloroform/pentane to provide 4 as
a red solid (50 mg, 95%). IR (ATR): 3026 (w), 2957 (s), 2865 (s), 1946 (s), 1006 (s), 792
(s), 713 (s) cm−1; UV–vis (CH2Cl2) λmax (ε): 245 (25 500), 415 (111 000), 534 (11 500),
1
569 (6 000) nm; H NMR (300 MHz, C6D6): δ 9.02 (s, 8H), 8.21 (d, J = 9.8 Hz, 4H), 8.18
(d, J = 9.9 Hz, 4H), 7.59 (d, J = 7.9 Hz, 4H), 7.54 (d, J = 7.9 Hz, 4H), 4.96 (t, J = 7.5 Hz,
1H), 4.36 (t, J = 7.3 Hz, 2H), 1.88 (d, J = 5.1 Hz, 2H), 1.42 (s, 36H); 13C NMR (75 MHz,
C6D6): δ 181.4, 150.5, 145.0, 144.6, 140.8, 135.4, 134.7, 133.0, 124.4, 123.8, 122.8, 121.6,
35.0, 31.9; ESI HRMS (CH2Cl2/MeCN) Calcd for C66H65N5O102Ru ([M]+) m/z 1045.4227,
found 1045.4256.
2.2.2. Synthesis of pentacene–porphyrin dyads 1 and 2.
2.2.2.1. General procedure. A Schlenk flask was charged with either pyridyl-substituted
pentacene derivative 1 or 2 (1 equiv) and RutBuPP·H2O 3 (1 equiv). Dry, deoxygenated
benzene (5 mL) was added and the solution was stirred for 1 h at rt. The mixture was
heated to 50 °C and stirred for 2 h at that temperature. The reaction mixture was cooled to
rt and the solvent was removed under reduced pressure. The solid purple residue was redis-
solved in minimal amount of dry, deoxygenated methylene chloride and precipitated by
addition of a large amount of dry, deoxygenated hexanes. The solids were filtered under N2
and dried in vacuo to provide the products as purple solids.
2.2.2.2. Dyad 5. Pentacene 1 (12 mg, 0.020 mmol) and RutBuPP·H2O 3 (20 mg,
0.020 mmol) were used according to the General Procedure. Complex 5 was obtained as a
purple solid (21 mg, 67%). M.p. > 400 °C; UV–vis (CH2Cl2) λmax (ε): 309 (210 000), 346
(13 300), 415 (200 000), 496 (5 350), 534 (18 700), 571 (11 400), 622 (11 600) nm; IR
1
(ATR): 3029 (w), 2953 (s), 2862 (s), 2123 (m), 1949 (s), 1262 (s), 1006 (s) cm−1; H NMR
(300 MHz, C6D6): δ 9.70 (s, 2H), 9.05 (s, 8H), 8.43 (s, 2H), 8.38 (d, J = 2.0 Hz, 2H), 8.35
(d, J = 2.0 Hz, 2H), 8.11 (d, J = 2.0 Hz, 2H), 8.09 (d, J = 1.9 Hz, 2H), 7.99 (d, J = 8.7 Hz,
2H), 7.53–7.40 (m, 11H), 7.31 (d, J = 2.1 Hz, 2H), 7.29 (d, J = 2.1 Hz, 2H), 6.80 (s, 1H),
5.62 (d, J = 8.2 Hz, 1H), 4.30 (dd, J = 8.3, 5.7 Hz, 1H), 2.42 (d, J = 2.4 Hz, 1H), 1.95 (dd,
J = 5.7, 1.2 Hz, 1H), 1.46–1.45 (m, 21H), 1.34 (s, 36H). ESI HRMS (CH2Cl2/MeOH)
Calcd for C101H98N8O102RuSi ([M]+) m/z 1568.6676, found 1568.6715; Calcd for
C61H60N4RuO ([M–1]+) m/z 966.3822, found 966.3830.
2.2.2.3. Dyad 6. Pentacene 2 (10 mg, 0.017 mmol) and RutBuPP·H2O 3 (17 mg,
0.017 mmol) were used according to the General Procedure. Complex 6 was obtained as a
purple solid (20 mg, 74%). UV–vis (CH2Cl2) λmax (ε): 309 (133 000), 348 (8 200), 415
(125 000), 496 (3 420), 534 (11 600), 571 (7 100), 622 (7 300) nm; IR (ATR): 2955 (s),
1
2863 (s), 1966 (s), 1609 (s), 1350 (s), 1006 (s), 715 (s) cm−1; H NMR (300 MHz, C6D6):
δ 9.62 (s, 2H), 9.10 (s, 8H), 8.43 (d, J = 2.0 Hz, 2H), 8.40 (d, J = 2.0 Hz, 2H), 8.27 (s,
2H), 8.22 (d, J = 2.0 Hz, 2H), 8.20 (d, J = 2.0 Hz, 2H), 7.90 (d, J = 8.4 Hz, 2H), 7.68 (d,
J = 2.0 Hz, 2H), 7.65 (d, J = 2.0 Hz, 2H), 7.59 (d, J = 2.0 Hz, 2H), 7.56 (d, J = 2.1 Hz,
2H), 7.51 (d, J = 8.4 Hz, 2H), 7.03–6.88 (m, 5H), 6.30 (s, 1H), 4.72 (d, J = 7.1 Hz, 2H),
1.86 (d, J = 7.1 Hz, 2H), 1.42 (bs, 36H), 1.37–1.36 (m, 21H); ESI HRMS (CH2Cl2/MeOH)
Calcd for C101H98N8O2102RuSi ([M–CO + MeOH]+) m/z 1572.6620, found 1572.6989.